(D, L)‐10‐Camphorsulfonic‐Acid‐Catalysed Synthesis of Diaryl‐Fused 2, 8‐Dioxabicyclo[3.3.1]nonanes from 2‐Hydroxychalcones and Naphthol Derivatives. Issue 2 (14th November 2013)

• Record Type: Journal Article
• Authors: Jiang, Xiaolong; Song, Zilan; Xu, Chang; Yao, Qizheng; Zhang, Ao
• Is Part Of: European journal of organic chemistry. Issue 2(2014)
• Page Start: 418
• Page End: 425
• Publication Date: 2013-11-14
• Subjects: Oxygen heterocycles -- Nitrogen heterocycles -- Cyclization -- Aromatic substitution -- Fused‐ring systems -- Acid catalysis; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201301295
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A tandem one‐pot Friedel–Crafts alkylation/double cyclization process to conveniently assemble diaryl‐fused 2, 8‐dioxabicyclo[3.3.1]nonanes with aryl substituents at the C‐1 position was developed. 2‐Hydroxychalcones and naphthol derivatives reacted in refluxing toluene with (D, L )‐10‐camphorsulfonic acid (CSA) as the catalyst. The transformation conveniently provided the corresponding 2, 8‐dioxabicyclo[3.3.1]nonanes fused with one phenyl and one naphthyl group in moderate to good yields, and various substitutions on both reaction partners were tolerated. More importantly, aryl‐ and aza‐aryl‐fused 2, 8‐dioxabicyclo[3.3.1]nonanes were prepared for the first time using this procedure. Abstract : An efficient approach to diaryl‐fused 2, 8‐dioxabicyclo[3.3.1]nonanes with aryl substituents at the C‐1 position was achieved. By using (D, L )‐10‐camphorsulfonic acid (CSA) as the catalyst, aryl‐ and aza‐aryl‐fused 2, 8‐dioxabicyclo[3.3.1]nonanes were prepared.